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Caribbean Holidays

Jamaica
 
Barbados
 
Anguilla
 
Antigua
 
Saint Lucia
 
British Virgin Islands
 
Puerto Rico
 
Cuba
 
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2 Free Nights
Calabash Hotel
From £1259 per adult
Was £ 1514, Saving £255
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50% Summer Sale
The Landings
From £1135 per adult
Was £ 1830, Saving £695
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2 Free Nights
Curtain Bluff
From £2135 per adult
Was £ 2860, Saving £725
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2 Free Nights
Ottley's Plantation Inn
From £1175 per adult
Was £ 1340, Saving £165
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Summer Offer
Cotton House
From £2095 per adult
Was £ 2834, Saving £739
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From Anguilla to St Lucia, Cuba to the Virgin Islands, Western & Oriental know all about Caribbean holidays and will help you select the perfect island to suit your personality. Formerly known as Tropical Locations, we have the ideal holiday destinations for families, couples or those travelling solo. Caribbean holidays are perfect for island hopping, honeymoons, sport or complete relaxation. There’s also the five-masted Royal Clipper for cruising if you want to see more of this region.

More than stunning beaches

Relaxation, nature and activity - you can find it on our Caribbean holidays. Acclaimed as one of the most beautiful destinations in the world the Caribbean offers more than stunning beaches.  Beautiful sea scapes, mountains, hills and waterfalls to admire – the scenery alone will charm you.

Above and below the sea

The calm waters of the Caribbean are perfect for yachters to sail.  But if your prefer underwater views and want a diving or snorkelling holiday, there’s a wealth of marine life in the warm waters for you to discover.  And if you want a more relaxing holiday, you’ll find natural hot springs to soak in. Plus our collection of luxury Caribbean holidays offers a selection of spa sanctuaries and yoga retreats.

Caribbean hospitality

The Caribbean is a culinary delight for those after a gastronomic feast and our holidays have been chosen for their cuisine, service and local charm – with warm and friendly greetings from the local people.

Western & Oriental's Beaches & Retreats

We’ve carefully selected a range of hotels from All Inclusive Caribbean holidays on popular islands like Antigua, Barbados and St Lucia, to hotels that are surrounded by the beauty of nature like those on Dominica and the Virgin Islands.

Caribbean Honeymoon Experiences

A string of idyllic beautiful beaches, warm turquoise waters and spectacular hospitality make this region the perfect place for a luxury honeymoon. From the vast shores of Barbados to the private villas in Turks & Caicos, each island offers a romantic escape giving you options for where to spend this special time in your life.

The Caribbean is one of the best regions if considering a multi-centre luxury honeymoon.
Start on the island of Saint Lucia. Known widely for the Pitons, its two dramatic peaks, much of the island is mountainous forest, deep valleys, and famous beautiful beaches. After a day or two in one of the luxury resorts in our collection, make your way over to Antigua. With its powder soft sand and reef protected waters, it is a beach-lover’s paradise. Considered to be the sunniest destination in the Caribbean you can spend your days laying in the sun or exploring the island sights such as the historic English harbour. Bask in the last days of your honeymoon on the lavish island of St. Barths. A haven of luxury, this small oasis is known for its sophisticated high-end shops, fine dining, and elegant scenery.

Our Caribbean specialists have years of experience travelling through the islands.  Call them today and they can help you choose your destination and tailor-make your holiday.

Read more about Caribbean

Total Holidays: 174       Page: 1 of 18 / View All
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Our holiday ideas section is to give you inspiration, for our entire luxury portfolio please see all hotels. If required please use the filters on the left to help define your search and contact our travel specialists for a tailor-made quote.
Windjammer Landing
Saint Lucia
Village-like resort in St Lucia with plenty of facilties, ideal for families, groups and couples!
  • All Inclusive
  • Beach / Retreat
  • Family
From £785 per adult
7 Nights, Room Only
Offer expires in 10 days
Special Offers
More Details
Blue Waters Inn
Tobago, Trinidad & Tobago
From the deep blue of the Atlantic, to the brilliant green of Tobago’s lush hills, Blue Waters Inn enjoys a picture perfect... read more
  • Beach / Retreat
From £905 per adult
7 Nights, Bed and Breakfast

More Details
Ti Kaye Resort and Spa
Saint Lucia
Turning off the main road and driving through woodland you eventually find yourself at Ti Kaye Resort and Spa, idyllically perched on a... read more
  • All Inclusive
  • Beach / Retreat
  • Honeymoons
From £925 per adult
7 Nights, Bed and Breakfast
Special Offers
More Details
Magdalena Grand Beach Resort
Tobago, Trinidad & Tobago
Set within a gated community, the resort features 200 rooms and suites, 3 swimming pools, 2 tennis courts and a children's club
  • All Inclusive
  • Beach / Retreat
From £935 per adult
7 Nights, Bed and Breakfast
Special Offers
More Details
Anse Chastanet
Saint Lucia
Possibly the most romantic hotel in the Caribbean, set amid 600 acres of tropical beachfront on the north side of Soufriere, with the... read more
  • Beach / Retreat
From £945 per adult
7 Nights, Bed and Breakfast
Offer expires in 10 days
Special Offers
More Details
Dreams La Romana Resort & Spa
La Romana
The Unlimited-Luxury® All Inclusive Dreams La Romana Resort & Spa is situated on the magnificent southeast coast of the Dominican... read more
  • All Inclusive
  • Beach / Retreat
  • Family
From £955 per adult
7 Nights, All Inclusive
Special Offers
More Details
Bacolet Beach Club
Tobago, Trinidad & Tobago
Twenty room intimate and relaxed hotel located on a hillside with a secluded beach below
  • Beach / Retreat
From £985 per adult
7 Nights, Bed and Breakfast
Special Offers
More Details
Little Good Harbour
Barbados
Little Good Harbour is an intimate all suite hotel, tucked away in the quiet fishing village of Shermans on the north-west coast. The focal... read more
  • Beach / Retreat
From £995 per adult
7 Nights, Room Only
Special Offers
More Details
Dreams Palm Beach
Punta Cana
Set on a 300 metre soft sand beach lined with palm trees is the family and couples friendly Dreams Palm Beach. With a fantastic... read more
  • All Inclusive
  • Beach / Retreat
  • Family
From £999 per adult
7 Nights, All Inclusive
Special Offers
More Details
Sugar Ridge
Antigua & Barbuda
Sugar Ridge is bordered by sugar cane and indigenous flora, and boasts spectacular views over Jolly Beach and towards Coco Beach with... read more
  • Honeymoons
From £1015 per adult
7 Nights, Bed and Breakfast
Offer expires in 10 days
Special Offers
More Details
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